Getting the right fit on dress shirts

So to start off, i don't have an average male build, so to speak. I workout and thus my chest sort of puffs out in relation to my stomach. As you'd imagine, this causes a whole whack of headaches when it comes to finding the right fitting shirt..

Heres the problem.

1. If I find a shirt that fits at the waist/midsection, the shirt gets super tight in the chest area

2. If i find a shirt that fits well on my chest, it ends up being too wide for my midsection.

Should I just find a slim/tailored fit shirt that can fit my chest, then tailor the midsection? have people ever done this before? because I haven't

Should I just find a slim/tailored fit shirt that can fit my chest, then tailor the midsection? have people ever done this before?

That doesn't seem too unreasonable. However before you try that, make sure you visit your tailor of choice and get their opinion on the matter (perhaps bring in a couple of your best fitting shirts). For example, some offer MTM shirts for the same price that your OTR shirt + alterations would cost you.

Depends on how severe the "drop" is (i.e. the difference between your chest and waist measurements. You can have your shirts darted by a tailor (at a reasonable cost usually). You can dart them yourself if you have a modicum of skill.

I just have my shirts tailored. I've gotten used to it. Ultimately you'll be happier this way. However, if you're patient and try a variety of labels, you may find a slim or tailored fit shirt that fits off of the rack.